Chicago Weekend Getaway – only have a few days in Chicago? Here is a list of things you MUST see and EAT! Plus a rooftop bar with the BESt view of Chicago! Add these places to your list!
At the end of June, we took a quick trip to Chicago. We haven’t been to Chicago in about 7 years! I can’t figure out why we stayed away so long? We had THE BEST time! I am already planning on going back next year.
The main purpose for our trip was to see Hamilton. Have you seen it? O-M-G! AMAZING! We both absolutely LOVED it. I highly recommend trying to snag a ticket when it goes on tour. I’m dying to see it again. It was 1000% worth the trip to Chicago.
We did a little sight seeing and a lot of eating. We found a rooftop bar with THE BEST views of Chicago and ate at one of the best restaurants EVER! I am really anxious to get back to The Windy City!
We dropped off our bags at the hotel and headed straight out in search of pizza.
There were three “famous” deep dish places within walking distance of our hotel.
I let Chicken Legs pick and he chose Uno.
We started with some cheese sticks.
I could eat my weight in these cheese sticks! SO good!!
We both got individual pizzas.
Chicken Legs got the Numero Uno
It was loaded with Sausage, Pepperoni, Onions, Peppers, Mushrooms, Chunky Tomato Sauce, Mozzarella And Romano.
I got the Prima Pepperoni and added sausage.
29 E Ohio St, Chicago, IL 60611
Phone: (312) 321-1000
After lunch we waddled down Michigan Avenue.
We stopped by The Bean.
201 E Randolph St, Chicago, IL 60602
Phone: (312) 742-1168
We passed this statue of Abraham Lincoln talking to Nick Saban about his play calling.
Just kidding! We really don’t know who the man with Lincoln is.
We asked some locals, and they didn’t know either.
We went with Saban, because it totally looks like him! LOL!
We had dinner reservations at a different restaurant in Chicago. After looking over all the reviews, we decided to ditch our original choice and go with tried-and-true Ditkas.
Our hotel was close enough that we could walk to dinner.
We started with the famous Pot Roast Nachos.
We got the small order. We could not stop eating these nachos!
Chicken Legs got a big fat steak for dinner.
I went with the Filet Sliders.
We shared the Chocolate Layer Cake for dessert.
00 E Chestnut St, Chicago, IL 60611
Phone: (312) 587-8989
Our hotel was literally next door to the Hancock Building.
We didn’t go up to the top on this trip.
We’ve been before, but will definitely add it our next itinerary.
I was SUPER excited to get to try Eataly on our trip.
Eataly is Mario Batali’s Italian market.
There are several restaurants and TONS of amazing Italian foods to purchase.
We ate the best Italian food of our lives here.
It was so good, that we ate here twice on our short trip!
Our first trip we ate at La Pizza & La Pasta.
We started with the Prosciutto and Fresh Mozzarella.
I’m still dreaming of this goodness!
The Cacio e Pepe (pasta with cheese and pepper) was to-die-for!
Finally we had some pizza. We built our own.
Rustica dough, San Marzano tomato sauce, Mozzarella di Bufala, Salame and Mushrooms.
It was crazy good! Wishing I had the leftovers right now!
On our second visit, we ate at La Piazza.
We started with an Arancini (fried risotto).
It came out looking like a pear. I’ve only had round arancini, so this was different.
This is the Ragu Arancini – Saffron risotto, bolognese, green peas, cacio di roma.
We shared a Roman-style pizza.
I wanted to see how it differed from the pizza the previous day.
We got the Amatriciana
Tomato sauce, crispy salumi, red onion, cacio di Roma cheese, chili flake
Delicious with a little kick.
I want to come back to eat dinner at some of the other restaurants in Eataly.
It was SO MUCH FUN!
We couldn’t pass up the Cannoli Bar.
This is the tiramisu cannoli. YUM!
We also got a fresh made crepe with Nutella and strawberries.
Basically, Eataly is my heaven on earth.
43 E Ohio St, Chicago, IL 60611
Phone: (312) 521-8700
Architecture River Tour
One of the architecture tours is a MUST when you are in Chicago.
There are several companies that offer tours, and I think they are pretty much the same.
This trip we toured with Shoreline Sightseeing at Navy Pier.
The boat was nice and the guide was great.
These honeycomb buildings are so fun!
LOVE the reflection!
LOVE this photo! I absolutely love all the reflections in the buildings.
This building has a map of Chicago on it.
The red dot is the location of this building.
You get great views of the Sears Tower/Willis Tower.
We didn’t make it over here to go to the observatory.
Chicago, you are SO colorful!
600 E Grand Ave, Chicago, IL 60611
Phone: (312) 222-9328
Gibson’s is our favorite steakhouse in Chicago.
This was the first dinner reservation we made after we booked out trip.
We started with the Carpaccio.
Chicken Legs got a gigantic steak!
He also got some Brussels Sprouts with bacon.
I opted for the filet.
It was cooked to perfection.
We also shared the Twice Baked Potato. SO good!
We couldn’t pass up one of their crazy big desserts.
Behold the Macadamia Turtle Pie – that is ice cream covered in macadamia nuts in a cookie crust smothered in chocolate.
Gibson’s Bar & Steakhouse
1028 N Rush St, Chicago, IL 60611
Phone: (312) 266-8999
The reason we came to Chicago.
It was fabulous. I highly recommend it!
The tickets were crazy expensive and worth every single penny.
Cindy’s Rooftop Bar
After the show, we walked straight to Cindy’s Rooftop Bar.
The bartender at the hotel recommended it to us and the recommendation was spot on.
How amazing are these views of Chicago?!?!
Since we were there, we enjoyed a cocktail with a view.
GO TO CINDY’S!!!
12 Michigan Avenue, Chicago, IL 60603
Phone: (312) 792-3502
Maple & Ash
This is another recommendation from the bartender at our hotel.
It was THE PLACE to be! The restaurant was hopping!
There is a bar downstairs and the restaurant is upstairs.
We started with the House Smoked Maple Glazed Bacon because – bacon!
It is on the menu as a side dish, but we just dove right in!
Chicken Legs got a Caesar Salad – wood-fired romaine, pecorino, soft cooked egg & savory sprinkles
He said it was THE BEST caesar salad he’s ever eaten.
He’s eaten a lot of caesar salad in his time, so that says a lot.
For his entree, Chicken Legs got the Australian Rack of Lamb.
He loved it!
We had to get the Au Gratin potatoes because I NEVER pass up au gratin potatoes.
For my entree, I went with the Prime Beef Meatballs.
They were served in caramelized tomato sauce with cheese curds & garlic bread.
It is an appetizer, but I definitely made a meal of it.
It was INSANELY delicious!
I want to fly to Chicago just to eat this again.
I’m not even joking.
Since we didn’t have much to eat already, we got dessert. LOL!
This is the Chocolate Banana Bulleit Bombe.
They pour warm Bulleit Bourbon Caramel on top of the chocolate domed dessert right at the table.
It was heavenly!
Maple & Ash is a new favorite. It is a MUST on your trip!
Maple & Ash
8 W Maple St, Chicago, IL 60610
Phone: (312) 944-8888
It is in the Watermark Place and next door to the Hancock building.
When we checked in, they upgraded us to a corner suite!!!!
I LOVE the Asprey products at The Ritz Carlton.
*might* steal them all to use at home.
We had two bathrooms in our room, so I stocked up!!!!
We had a great view from our room.
They were redoing the restaurant and rooftop bar while we were there.
We made the best of it.
The bartender, Mel, was great.
He is the one that told us about Cindy’s and Maple & Ash.
I drank lots of prosecco.
Chicken Legs likes to tell people that prosecco is my middle name. He thinks it’s funny.
I think some of them believe him. LOL!
We ate lunch in the restaurant before we headed to the airport.
The Chicken Club was great!
I can not wait to go back and see the newly renovated bar and restaurant.
It opened the week after our trip. Boo!!!
I guess that is our reason to go back to Chicago!
What are your favorite places to eat in Chicago?
Anything we MUST do on our next trip?
Leave me some suggestions!!!
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Lowry's…you HAVE to go. Expensive, but seriously the best prime rib ever!! They roll it to your table in a big cart and carve it for you. The chocolate paper bag dessert was awesome. That same weekend, we ate at Billy Goat Tavern (think Saturday Night Live—cheeburger, no coke–pepsi). And we also had brunch at Signature Room at the 95th–Hancock Bldg. Sooooo good!!
I live close to Chicago and usually take weekend trips at least once a month. You mentioned so many of our favorites. Chicago really is a beautiful city!
I spent 24 hours in Chicago last year and wish I could have fit in the boat architecture tour! All of this food looks amazing! I wish I had an Eatlay closer, I loved everything about it. Sounds like an amazing getaway!
We have been contemplating Chicago. We've never been. This post is definitely tempting us more! Do you have a hotel reccomendation?
Stephanie– great-sounding trip. Your "stuff" doesn't scroll down well for me. Is it my computer?
I would say that it is your computer- it scrolls fine on mine and no one else has had any issues.
We have so many favorites in Chicago. We always to go the Purple Pig. And we love Twin Anchors Ribs. Last trip we went out to Wicker Park and tried Big Star Tacos. It's a Paul Kahan restaurant. The food is great, and the atmosphere is so fun. Across the street is a hidden bar, The Violet Hour. The front of the building is covered in graffiti, and there is just a single door with a doorman that stands outside to let you in. Y'all should check it out!